Journal of Organic Chemistry 2008-09-05

An application of borane as a protecting group for pyridine.

Matthew A Zajac

Index: J. Org. Chem. 73(17) , 6899-901, (2008)

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Abstract

Efforts to couple 4 with 12 employing base mediation are problematic due to the formation of 6. To circumvent this issue, 12 was converted to the pyridine borane complex (13). Alkylation of 4 with 13 provided 3 after removal of the borane under acidic conditions and saponification of the ester.